Utilize este identificador para referenciar este registo: http://hdl.handle.net/10400.1/4237
Título: 3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-dioxide: unusual C—O—C ether bond lengths and reactivity
Autor: Barkley, J. V.
Cristiano, Maria Lurdes Santos
Johnstone, Robert A. W.
Loureiro, Rui M. S.
Data: 1997
Editora: International Union of Crystallography
Citação: Barkley, J. V.; Cristiano, M. L. S.; Johnstone, R. A. W.; Loureiro, R. M. S. 3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-Dioxide: Unusual C—O—C Ether Bond Lengths and Reactivity, Acta Crystallographica Section C Crystal Structure Communications, 53, 3, 383-386, 1997.
Resumo: Ethers such as the title compound, C~HIINO3S, (1), rearrange thermally to give N-allyl isomers, (2), in high yield. The X-ray structure determination of the title ether shows a central C--O--C linkage which has one very short (notional) C--O single bond and one exceptionally long single C--O bond. The thermal migration of allyl from the O to the N atom involves the breaking of one of the ether bonds in (1) and a shortening of the other as it becomes a formal carbonyl group in the product (2). The rearrangement is thus considerably assisted by the ground-state structure of the starting ether, in which the bond to be broken is already stretched and the one that is to form a carbonyl group is already a substantial partial double bond.
Peer review: yes
URI: http://hdl.handle.net/10400.1/4237
ISSN: 0108-2701
Aparece nas colecções:CCM2-Artigos (em revistas ou actas indexadas)

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